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Highly Efficient Biocatalytic Resolution of cis ‐ and trans ‐3‐Aminoindan‐1‐ol: Syntheses of Enantiopure Orthogonally Protected cis ‐ and trans ‐Indane‐1,3‐diamine
Author(s) -
LópezGarcía Mónica,
Alfonso Ignacio,
Gotor Vicente
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200306070
Subject(s) - enantiopure drug , indane , chemistry , diastereomer , candida antarctica , enantiomer , mitsunobu reaction , diamine , stereochemistry , organic chemistry , lipase , enantioselective synthesis , enzyme , catalysis
The efficient chemoenzymatic synthesis of enantiopure 1,3‐difunctionalized indane derivatives has been achieved. The corresponding cis and trans N ‐protected amino alcohols were successfully resolved by acetylation using lipase B, which is a biocatalyst isolated from Candida antarctica . All the possible isomers were obtained in very good chemical yields and ee values (>99 %). The utility of these compounds was subsequently shown by the preparation of orthogonally protected cis ‐ and trans ‐indane‐1,3‐diamine using a Mitsunobu reaction. Both enantiomers of the trans isomer and a desymmetrized cis diastereomer were prepared in enantiopure form. Complete inversion of configuration during the Mitsunobu reaction was demonstrated by a combination of NMR techniques and molecular modeling. The utility and versatility of the strategy was also demonstrated by the selective deprotection of each nitrogen atom under mild reaction conditions.